The film begins with Oliver (Ewan McGregor) cleaning out his parents house with his dog (a Jack Russell named Cosmo). Oliver explains to the audience that a couple of months after his Mother, Georgia (played by Mary Page Keller), has passed his father, Hal (played by Christopher Plummer), came out to him and told Oliver that he was gay. Oliver always thinks of his father wearing a purple shirt when he told him this when in reality he wore a plaid robe.

Oliver works as a cover artist (literally someone who makes art pieces for the cover of bands albums etc.). Oliver draws pictures of a couple of the five serious relationships he's had in the past. While driving his friends, Elliot and Shauna (Kai Lennox and China Shavers), to his house his friends recall a time when Oliver was fun and not so doom and gloomy. The next scene we see Oliver dressed up as Sigmund Freud and his friends dressed up in costumes, as well. Oliver tells his dog that he's leaving and hesitantly closes the door, but while he tries to walk away, the dog howls sadly and the next scene is of Oliver holding Cosmo while Elliot drives. At the party Oliver, dressed as Freud, sits over a man dressed up as Frankenstein. While holding Cosmo Oliver hears Frankenstein talk about his problems with his mother and wife and then Frankenstein leaves thanking the doctor for his help. Just as Frankenstein leaves a women dressed as Charlie Chaplin, sits down. Oliver tells her that he was just about to take a break, but when she doesn't verbally respond back he eases back into his chair and starts to ask her questions about her mother, her life and what's on her mind. The woman (whose name we later find out is Anna played by Mèlanie Laurent) takes out a memo pad and a pen and writes, "Why are you so sad?" Oliver is taken aback and asks how she knows. She draws eyes on the memo pad. Intrigued Oliver tells her to wait on the couch while he gets them something to drink. When he gets back, they talk and exchange numbers. While Oliver is leaving with Jack, he gets a phone call. Oliver says hello, but no one answers. He's about to hang up when he hears a beep on the other end. He figures out that this is Anna. He starts asking her questions and she answers by either pressing a button once or twice. They end up meeting outside the party and get in Oliver's car. Anna points to the direction and Oliver drives, even driving on the sidewalk sometimes. They go to Anna's hotel room. We learn that Anna is an actress who will only be in LA for a few days. Anna Oliver sleep together.

While Oliver's storyline is being told, the film also tells the story of Hal. Oliver explains to us that Hal grew up in a time where gay men had sex in bathroom stalls and were jailed if their sexual orientation were revealed. Hal always knew he was gay but married Georgia (who also knew of Hal's sexual orientation) as somewhat of a last resort to be 'cured'. There are several scenes of Hal and Georgia's daily morning kiss where Hal leaves and Georgia stands a few seconds afterwards usually looking dissatisfied. After the kiss, Georgia goes into a young Oliver's rooms and 'shoots' him with her hand and encourages him to die in a bigger way. On day Georgia tells young Oliver that it's okay to scream in his room if he needs to, when he doesn't Georgia assures him that one day he'll need to. Georgia takes young Oliver to the art museum where Hal works. At one event, Georgia is so fed up with the women who frequent the museum that she insults them and when she and young Oliver are in the car she tells him to point to a direction and she drives, even driving on the sidewalk.

Oliver and Anna become closer. Oliver learns that Anna has a fractured relationship with her Father who keeps calling the phone that Anna never picks up because she knows it's him. Anna learns that Oliver's father has passed away and came out to him just a few months before dying (Oliver meets Anna months after Hal passes away). The dog also likes Anna and in subtitles keeps asking Oliver: are we married yet? Oliver and Anna go on adventures together from rollerskating in her hotel to spray painting on the highways of the city with Elliot and Shauna.

We again flashback to Hal and his growing interest to embrace his sexuality, his growing participation in the LGBT community, and his dating life. Hal starts to date Andy (Gorgan Visnjic). A young man who is into older men and has father issues of his own. There is a slight tension between Andy and Oliver, and Andy believes that Oliver might be a little homophobic, but Oliver is a little miffed that Hal is having a relationship with Andy who is seeing other men and would rather his father be in a monogamous relationship with a guy who is 'the one', but Hal fears that Oliver will be miserable and wait forever for 'the one' instead being happy with someone who is 'the right now'. Hal is getting over a hospitalization and goes in for a check-up. The doctor tells him that he has cancer that is terminal and that he is going to die. Hal lies to his friends and tells them that the doctor told him that he is fine. Hal does not want to tell Andy when Oliver thinks he should, Oliver goes to tell Andy about Hal's illness, but before he does Andy tells Oliver that he really cares about Hal. Oliver is unable to tell Andy.

Oliver reflects on his father's life, and how much happier he was later in his life. He decides to ask Anna to move in with him. She accepts, and they move in together, but things do not run smoothly. Oliver gives Anna drawer space which she never fills and stills lives out of her suitcase. Anna and Oliver become distant. Their easy conversation becomes stilted, and they become awkward with each other. They have a conversation and Oliver doesn't think he should be feeling the way he's feeling. They break up, and Oliver watches as Anna moves out and gets into a cab.

Oliver realizes he made a mistake and decides to go to Anna's apartment in New York. He drops off Cosmo at Elliot's house, but Cosmos howls and Oliver feels guilty. He then drops off Cosmo at Andy's house. Cosmo jumps into Andy's arm, and you can tell Andy missed Cosmo (since Cosmo was originally Hal's dog). Oliver is New York and knocks on Anna's door. When she doesn't answer he calls her. She is still in LA in her hotel room. She tells him where to get a spare key and guides him through her apartment through her phone.

Back in LA Oliver shows Anna Hal's personal ad that he put out for himself to look for men. Anna and Oliver tell each other that there new in this aspect of love. It is implied that they are back together. Oliver looks at Anna, and they both question what to do next.